(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->4)-6-azido-2,3-di-O-benzoyl-6-deoxy-α-D-galactopyranosyl chloride | 260976-56-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->4)-6-azido-2,3-di-O-benzoyl-6-deoxy-α-D-galactopyranosyl chloride
• CAS: 260976-56-5
• 化学式: C₅₄H₅₂ClN₃O₁₁
• 分子量: 954.473
• InChiKey: MAMFEIURGCITDW-JYQLOIQVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.79
• 重原子数：
  69.0
• 可旋转键数：
  21.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  165.97
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-β-D-glucopyranoside 、 (2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->4)-6-azido-2,3-di-O-benzoyl-6-deoxy-α-D-galactopyranosyl chloride 在 3 A molecular sieve 、 silver trifluoromethanesulfonate 、 1,1,3,3-四甲基脲 作用下， 以 二氯甲烷 为溶剂， 反应 21.0h， 以52%的产率得到2-(trimethylsilyl)ethyl (2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->4)-(6-azido-2,3-di-O-benzoyl-6-deoxy-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of selected aminodeoxy analogues of galabiose and globotriose

  摘要：

  Six aminodeoxy 2-(trimethylsilyl)ethyl (Me3SiEt) glycoside analogues of galabiose (4'- and 6'-aminodeoxy) and globotriose (6 "-, 4 "-, 2 "-, and 6'-aminodeoxy) were synthesized by glycosylation of protected Me3SiEt galactoside and lactoside accepters with azido-substituted monosaccharide donors, followed by reduction of the azido groups and removal of the protecting groups. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00229-3
• 作为产物：
  描述：

  (2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->4)-6-azido-2,3-di-O-benzoyl-6-deoxy-D-galactopyranose 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以100%的产率得到(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->4)-6-azido-2,3-di-O-benzoyl-6-deoxy-α-D-galactopyranosyl chloride
  参考文献：
  名称：

  Synthesis of selected aminodeoxy analogues of galabiose and globotriose

  摘要：

  Six aminodeoxy 2-(trimethylsilyl)ethyl (Me3SiEt) glycoside analogues of galabiose (4'- and 6'-aminodeoxy) and globotriose (6 "-, 4 "-, 2 "-, and 6'-aminodeoxy) were synthesized by glycosylation of protected Me3SiEt galactoside and lactoside accepters with azido-substituted monosaccharide donors, followed by reduction of the azido groups and removal of the protecting groups. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00229-3